WO2003040159A3 - Bidentate ligands for the carbonylation of unsaturated compounds - Google Patents

Bidentate ligands for the carbonylation of unsaturated compounds Download PDF

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Publication number
WO2003040159A3
WO2003040159A3 PCT/EP2002/012380 EP0212380W WO03040159A3 WO 2003040159 A3 WO2003040159 A3 WO 2003040159A3 EP 0212380 W EP0212380 W EP 0212380W WO 03040159 A3 WO03040159 A3 WO 03040159A3
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbonylation
unsaturated compounds
bidentate ligands
catalyst
Prior art date
Application number
PCT/EP2002/012380
Other languages
French (fr)
Other versions
WO2003040159A8 (en
WO2003040159A2 (en
Inventor
Eit Drent
Ginkel Roelof Van
Der Made Renata Helena Van
Original Assignee
Shell Int Research
Eit Drent
Ginkel Roelof Van
Der Made Renata Helena Van
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Int Research, Eit Drent, Ginkel Roelof Van, Der Made Renata Helena Van filed Critical Shell Int Research
Priority to US10/494,901 priority Critical patent/US7135542B2/en
Priority to EP02790337A priority patent/EP1444241B1/en
Priority to CA002466252A priority patent/CA2466252A1/en
Priority to JP2003542204A priority patent/JP2005508390A/en
Priority to DE60206521T priority patent/DE60206521T2/en
Priority to AT02790337T priority patent/ATE305936T1/en
Priority to AU2002363378A priority patent/AU2002363378A1/en
Publication of WO2003040159A2 publication Critical patent/WO2003040159A2/en
Publication of WO2003040159A8 publication Critical patent/WO2003040159A8/en
Publication of WO2003040159A3 publication Critical patent/WO2003040159A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1895—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/38—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes
    • C07C2/40—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes of conjugated dienes
    • C07C2/403—Catalytic processes
    • C07C2/406—Catalytic processes with hydrides or organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C07D201/02—Preparation of lactams
    • C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5027—Polyphosphines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24—Phosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
    • C07C2531/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of the platinum group metals, iron group metals or copper

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyamides (AREA)

Abstract

Bidentate ligand of formula (I), R1R2M1-R-M2R3R4 wherein M1 and M2 each indenpendently represent P, As or Sb; R1, R2, R3 and R4 each independently represent the same or a different optionally substituted organic group and at least one of R1, R2, R3 and R4 contains a tertiary carbon atom through which the group is linked to M1 or M2; and R represents a bridging group based on a trimethylene group connecting M1 and M2 of which the middle carbon atom is double bonded to a non-metal element chosen from group 14, 15 or 16 of the periodic table of elements. Catalyst comprising this bidentate ligand and carbonylation process n which this catalyst is used.
PCT/EP2002/012380 2001-11-09 2002-11-05 Bidentate ligands for the carbonylation of unsaturated compounds WO2003040159A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US10/494,901 US7135542B2 (en) 2001-11-09 2002-11-05 Bidentate ligands for the carbonylation of unsaturated compounds
EP02790337A EP1444241B1 (en) 2001-11-09 2002-11-05 Bidendate ligands for the carbonylation of unsaturated compounds
CA002466252A CA2466252A1 (en) 2001-11-09 2002-11-05 Bidentate ligands for the carbonylation of unsaturated compounds
JP2003542204A JP2005508390A (en) 2001-11-09 2002-11-05 Bidentate ligands for carbonylation of unsaturated compounds.
DE60206521T DE60206521T2 (en) 2001-11-09 2002-11-05 BIDENTATE LIGANDS FOR THE CARBONYLATION OF UNSATURATED COMPOUNDS
AT02790337T ATE305936T1 (en) 2001-11-09 2002-11-05 BIDENTATE LIGANDS FOR THE CARBONYLATION OF UNSATURATED COMPOUNDS
AU2002363378A AU2002363378A1 (en) 2001-11-09 2002-11-05 Bidentate ligands for the carbonylation of unsaturated compounds

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US34820501P 2001-11-09 2001-11-09
US60/348,205 2001-11-09
EP02077923 2002-07-18
EP02077923.7 2002-07-18

Publications (3)

Publication Number Publication Date
WO2003040159A2 WO2003040159A2 (en) 2003-05-15
WO2003040159A8 WO2003040159A8 (en) 2003-07-31
WO2003040159A3 true WO2003040159A3 (en) 2004-01-08

Family

ID=26077604

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/012380 WO2003040159A2 (en) 2001-11-09 2002-11-05 Bidentate ligands for the carbonylation of unsaturated compounds

Country Status (13)

Country Link
US (1) US7135542B2 (en)
EP (1) EP1444241B1 (en)
JP (1) JP2005508390A (en)
KR (1) KR20050043775A (en)
CN (1) CN1308337C (en)
AT (1) ATE305936T1 (en)
AU (1) AU2002363378A1 (en)
CA (1) CA2466252A1 (en)
DE (1) DE60206521T2 (en)
ES (1) ES2250728T3 (en)
MY (1) MY134247A (en)
TW (1) TWI262102B (en)
WO (1) WO2003040159A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2500095C (en) * 2002-09-26 2011-10-18 Shell Internationale Research Maatschappij B.V. Process for the hydroformylation of an ethylenically unsaturated compound
GB0403592D0 (en) 2004-02-18 2004-03-24 Lucite Int Uk Ltd A catalyst system
US7265242B2 (en) * 2004-02-26 2007-09-04 Shell Oil Company Process for the carbonylation of ethylenically or acetylenically unsaturated compounds
MY154959A (en) 2005-11-17 2015-08-28 Lucite Int Uk Ltd Carbonylation of ethylenically unsaturated compounds
AU2007327051B2 (en) 2006-12-02 2013-07-04 Lucite International Uk Limited Novel carbonylation ligands and their use in the carbonylation of ethylenically unsaturated compounds
EP1992677A1 (en) * 2007-05-10 2008-11-19 Castrol Limited Lubricant composition for combustion engine containing dispersant additive and polymer dispersant viscosity index improver
SI2252698T1 (en) * 2008-03-11 2018-04-30 Genomatica, Inc. Adipate ester or thioester synthesis
GB201000078D0 (en) 2010-01-05 2010-02-17 Lucite Int Uk Ltd Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands
DE102011089008B4 (en) * 2011-12-19 2017-08-24 Evonik Degussa Gmbh Process for the preparation of esters of formates and olefinically unsaturated compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998042717A1 (en) * 1997-03-26 1998-10-01 Shell Internationale Research Maatschappij B.V. Diphosphines
WO2001072697A2 (en) * 2000-03-14 2001-10-04 Shell Internationale Research Maatschappij B.V. Process for the carbonylation of pentenenitrile
WO2001087899A1 (en) * 2000-05-17 2001-11-22 Shell Internationale Research Maatschappij B.V. Bidentate ligands useful in catalyst system

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19840253A1 (en) 1998-09-03 2000-03-09 Basf Ag Process for the preparation of cyanvaleric acid or esters
MY127358A (en) * 2000-03-14 2006-11-30 Shell Int Research Process for the carbonylation of ethylenically unsaturated compounds
CA2476742A1 (en) * 2002-02-19 2003-08-28 Shell Internationale Research Maatschappij B.V. Processes for the preparation of a carobxylic anhydride and use of the carboxylic anhydride as an acylation agent
US7084089B2 (en) * 2002-07-31 2006-08-01 Shell Oil Company Process for the carbonylation of ethylenically unsaturated compounds, bidentate diphosphine composition used in this process and a process for preparation of this bidentate diphosphine composition
US7265242B2 (en) * 2004-02-26 2007-09-04 Shell Oil Company Process for the carbonylation of ethylenically or acetylenically unsaturated compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998042717A1 (en) * 1997-03-26 1998-10-01 Shell Internationale Research Maatschappij B.V. Diphosphines
WO2001072697A2 (en) * 2000-03-14 2001-10-04 Shell Internationale Research Maatschappij B.V. Process for the carbonylation of pentenenitrile
WO2001087899A1 (en) * 2000-05-17 2001-11-22 Shell Internationale Research Maatschappij B.V. Bidentate ligands useful in catalyst system

Also Published As

Publication number Publication date
TW200401670A (en) 2004-02-01
EP1444241B1 (en) 2005-10-05
MY134247A (en) 2007-11-30
EP1444241A2 (en) 2004-08-11
KR20050043775A (en) 2005-05-11
ES2250728T3 (en) 2006-04-16
CN1596261A (en) 2005-03-16
US7135542B2 (en) 2006-11-14
ATE305936T1 (en) 2005-10-15
TWI262102B (en) 2006-09-21
WO2003040159A8 (en) 2003-07-31
JP2005508390A (en) 2005-03-31
AU2002363378A1 (en) 2003-05-19
US20040259724A1 (en) 2004-12-23
CA2466252A1 (en) 2003-05-15
DE60206521D1 (en) 2006-02-16
CN1308337C (en) 2007-04-04
DE60206521T2 (en) 2006-06-14
WO2003040159A2 (en) 2003-05-15

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